Let’s face it, a lot of people have sent an e-mail, only to wish it could somehow be unsent. Maybe it was a mistake, something embarrassing, a rant, or whatever. Think twice before hitting the Send button on those sensitive e-mails.


I recall the time one of my users came to me, almost in a panic, asking if there was a way to retrieve an e-mail that was sent to everyone in the office before the recipients opened it. “Well, it depends,” I said. I was told that it was just sent a moment ago, and the mistake was realized just as the Send button was hit. It turns out that instead of a Reply to sender, this person Replied to All — with some rather sensitive information contained within the e-mail.

The good news was that as a small office, there weren’t that many accounts to check. The bad news was that I used an outside provider as an e-mail host, so I would have to log in to each e-mail account separately to look for the e-mail. We could only hope that I could retrieve the e-mail from each account before their Outlook clients automatically downloaded it — and some people probably had it configured to check every 5 minutes or so.

I guess luck was on our side that day, as I was able to log in to everyone’s e-mail account and delete the e-mail before it was downloaded by anyone’s Outlook client. Otherwise, there would have been nothing I could have done. My advice was obvious — double-check what you’re doing before hitting that Send button.

And if I could segue into another type of e-mail, I’ll include those rant e-mails as well. I will admit that I’ve written one or two in my life, but I always take pause before I send it.

Back in the day of the written letter, people might have been advised to put certain types of letters in a desk drawer for a few days before mailing it — you know, the emotional ones, the accusatory ones, or anything that might serve to offend or upset the recipient. The thought being, of course, that if you think about what you wrote for a few days, you might decide that discretion really is the better part of valor and that you should throw it in the trash instead of in the mailbox.

Regarding rant e-mails, I actually have a good friend who I use as a rant buddy. Whenever I write one of those types of e-mails, I send it to him instead of the people to whom it was written. We have this understanding between us that it’s better to bounce a rant off of each other instead of sending it to someone for whom it was really written. Not only is that a good way to put a letter into the cyber desk drawer, but, without exception, they always provide a good laugh between the two of us. The last time I sent him one of my rants, his reply the next day was “Cool rant dude.” Of course, the rant went no further, but I was still able to get it out of my system by writing the e-mail. Writing a rant is one thing — and it oftentimes provides some self-satisfaction by simply writing it — but sending it is another.

Anyway, borrowing from that old carpenter’s adage “measure twice, cut once,” when it comes to sending sensitive e-mails, be sure to think twice or check twice before hitting that Send button once. And, if you just have to send that rant to someone, consider getting yourself a rant buddy. It will surely allow you to get something off your chest one day and provide loads of laughs the next.

Feel free to share your thoughts or similar e-mail stories in the following discussion.